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WO2009115152A1 - Procédé de fabrication d'épichlorhydrine - Google Patents

Procédé de fabrication d'épichlorhydrine Download PDF

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Publication number
WO2009115152A1
WO2009115152A1 PCT/EP2008/067584 EP2008067584W WO2009115152A1 WO 2009115152 A1 WO2009115152 A1 WO 2009115152A1 EP 2008067584 W EP2008067584 W EP 2008067584W WO 2009115152 A1 WO2009115152 A1 WO 2009115152A1
Authority
WO
WIPO (PCT)
Prior art keywords
mixture
hydrogen peroxide
allyl chloride
reaction
reaction stage
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2008/067584
Other languages
German (de)
English (en)
Inventor
Willi Hofen
Claudia Brasse
Robert Franke
Robert Katzer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Priority to US12/919,637 priority Critical patent/US8481765B2/en
Priority to ES08873464T priority patent/ES2379311T3/es
Priority to EP08873464A priority patent/EP2285791B1/fr
Priority to CN2008801281503A priority patent/CN101983192B/zh
Priority to BRPI0822343-2A priority patent/BRPI0822343A2/pt
Priority to HK11105877.4A priority patent/HK1152034B/xx
Priority to PL08873464T priority patent/PL2285791T3/pl
Priority to AT08873464T priority patent/ATE548361T1/de
Priority to AU2008353129A priority patent/AU2008353129B2/en
Priority to JP2011500055A priority patent/JP5615797B2/ja
Publication of WO2009115152A1 publication Critical patent/WO2009115152A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency

Definitions

  • the invention relates to a process for the preparation of epichlorohydrin by reacting allyl chloride with hydrogen peroxide.
  • Epichlorohydrin Chlormethyloxiran
  • z. B. is used for the production of resins.
  • allyl chloride is usually contaminated with 1-chloropropane and / or 2-chloropropane. Both impurities have similar boiling points as allyl chloride:
  • a method according to the invention in which, in a first reaction stage, a chloropropane-containing allyl chloride is reacted in excess with hydrogen peroxide.
  • the unreacted allyl chloride is separated and recycled to the reaction wherein a portion of the separated allyl chloride is fed to a second reaction stage and reacted with hydrogen peroxide, the amount of hydrogen peroxide in the second reaction stage being selected to substantially and preferably substantially fully react the allyl chloride , From the reaction mixture of the second reaction stage, the chloropropanes can then be separated by distillation without losses of allyl chloride.
  • a chloropropane-containing allyl chloride is reacted in excess with hydrogen peroxide.
  • the unreacted allyl chloride is separated and recycled to the reaction wherein a portion of the separated allyl chloride is fed to a second reaction stage and reacted with hydrogen peroxide, the amount of hydrogen peroxide in the second reaction stage being selected to substantially and preferably substantially fully react the
  • the invention therefore relates to a process for the preparation of epichlorohydrin, in which
  • reaction mixture formed in the first reaction stage is separated in a distillation into a mixture (A), the unreacted allyl chloride, and 1-chloropropane and / or
  • the mixture (A2) is reacted in a second reaction stage with hydrogen peroxide in the presence of a titanium-containing zeolite catalyst in a molar ratio of allyl chloride to hydrogen peroxide in the range from 0.5: 1 to 1.25: 1,
  • reaction mixture formed in the second reaction stage is separated in a distillation into a mixture (C) which contains 1-chloropropane and / or 2-chloropropane and a mixture (D) which contains epichlorohydrin and
  • the mixture (C) is removed from the process.
  • allyl chloride and hydrogen peroxide are reacted in the presence of a titanium-containing zeolite catalyst to form epichlorohydrin.
  • the allyl chloride used contains 1-chloropropane and / or 2-chloropropane.
  • Technical grades of allyl chloride which contain 1-chloropropane and / or 2-chloropropane as by-products of the industrial production of allyl chloride can therefore be used for the process according to the invention.
  • the content of 1-chloropropane and 2-chloropropane in the allyl chloride used is preferably in the range of 0.01 to 2 wt .-%, particularly preferably in the range of 0.05 to 0.8 wt .-%.
  • Hydrogen peroxide can be used as an aqueous solution, which preferably has a content of hydrogen peroxide in the range from 1 to 90% by weight, particularly preferably from 10 to 80% by weight and in particular from 30 to 70% by weight. Hydrogen peroxide can be used as a commercially available, stabilized solution. Also suitable is the non-stabilized hydrogen peroxide prepared by the anthraquinone process, which can be used without further purification.
  • a hydrogen peroxide known from WO 2004/028962 which contains less than 50 ppm of alkali metals and alkaline earth metals, less than 50 ppm of bases having a pK B of less than 4.5 and at least 100 ppm of anions, in each case based on the weight of hydrogen peroxide. contains.
  • a solution of hydrogen peroxide in methanol is used, which was preferably prepared by reacting hydrogen and oxygen over a palladium catalyst in methanol.
  • a palladium catalyst particularly preferred is a
  • a hydrogen peroxide solution in methanol according to claim 9 of WO 2006/108784 which contains 2 to 15% by weight of hydrogen peroxide, 0.5 to 20% by weight of water, 60 to 95% of hydrogen peroxide Wt .-% methanol, 10 6 to 10 2 mol / 1 bromide, and 10 6 to 0.1 mol / 1 dimethyl sulfate and / or monomethyl sulfate.
  • titanium-containing zeolite catalyst it is possible to use all of the titanium-containing zeolites known from the prior art which have a catalytic activity for the reaction of olefins with hydrogen peroxide.
  • the titanium-containing zeolite catalyst used is preferably a titanium silicalite having an MFI or MEL crystal structure. Particular preference is given to using titanium silicalites of the composition (TiO 2 ) x (SiO 2 ) i- x , where x im
  • titanium silicalites which have been prepared by the process according to WO 01/64581 or the process according to WO 01/64582.
  • the titanium-containing zeolite catalyst can in the process according to the invention in the form of a
  • Suspension catalyst can be used.
  • the reaction is preferably carried out so that the catalyst suspended in the reaction mixture is retained in the first reaction stage, for example by filtration or by sedimentation, so that the
  • Reaction mixture which is separated in step b) in a distillation, contains no catalyst.
  • the titanium-containing zeolite catalyst is used in the process of the invention in the form of a fixed bed catalyst.
  • Particularly suitable are extrusion-formed fixed-bed catalysts in the form of extrudates having a diameter of 1 to 5 mm, preferably a binder in an amount of 1 to 99 wt .-%, particularly preferably 1 to 40 wt .-%, based on the titanium-containing Contain zeolite.
  • All the binders which react under the reaction conditions neither with the hydrogen peroxide used nor with the epichlorohydrin formed are suitable.
  • Particularly suitable binders are silicic acids.
  • fixed bed catalysts in which a fumed silica, a colloidal silica sol or a tetraalkyl orthosilicate or a combination of two of these components have been used as precursors for the binder.
  • fixed-bed catalysts which have been prepared by the process known from WO 01/72419 by shaping a molding composition which has a plateau value of the Curve curve in the range from 20 to 90 mm.
  • step a) in the first reaction stage allyl chloride
  • the molar ratio of allyl chloride to hydrogen peroxide can be up to 100: 1.
  • the molar ratio is in the range of 1.5: 1 to 5: 1.
  • the molar ratio of allyl chloride to hydrogen peroxide is particularly preferably 2: 1 to 4: 1.
  • the selectivity for epichlorohydrin decreases in the first reaction stage.
  • Higher molar ratios have the disadvantage that large amounts of unreacted allyl chloride must be separated and recycled with a corresponding expenditure of energy.
  • step d) of the process according to the invention in the second reaction stage allyl chloride and
  • the molar ratio of allyl chloride to hydrogen peroxide is 0.8: 1 to 1.15: 1.
  • the use of a molar ratio in these ranges makes it possible to completely or largely convert allyl chloride in the second reaction stage, so that the mixture (C) obtained in step e) and removed from the process in step f) only contains a small proportion of the allyl chloride used.
  • the reaction of allyl chloride and hydrogen peroxide is carried out in steps a) and d), preferably in the presence of a solvent.
  • a solvent particularly suitable solvents are those which dissolve allyl chloride and hydrogen peroxide under the reaction conditions and do not react or react only to a small extent with hydrogen peroxide or epichlorohydrin.
  • Suitable solvents include, for example, alcohols, such as methanol, ethanol or tert-butanol; Glycols such as ethylene glycol, 1, 2-propanediol or 1, 3-propanediol; cyclic ethers, such as tetrahydrofuran or dioxane; Glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether or propylene glycol monomethyl ether; and ketones such as acetone or 2-butanone.
  • Preferred solvents are aliphatic alcohols having 1 to 4 carbon atoms. Most preferably, methanol is used as the solvent.
  • the proportion of solvent in the reaction mixture in the first reaction stage is preferably 10 to 95 wt .-%, particularly preferably 30 to 80 wt .-% and in the second reaction stage, preferably 10 to 95 wt .-%, particularly preferably 30 to 80 wt .-%.
  • the reaction of allyl chloride and hydrogen peroxide is carried out in the first reaction stage preferably at a temperature in the range of 0 0 C to 100 0 C, more preferably 30 0 C to 65 ° C and in the second reaction stage, preferably at a temperature in the range of 0 0 C. to 100 0 C, more preferably 30 0 C to 65 ° C.
  • the pressure in the reaction stages can be freely chosen within wide limits and is preferably chosen so high that the boiling point of allyl chloride at the pressure used is equal to or higher than the reaction temperature used.
  • the reaction conditions are preferably chosen in the first reaction stage so that a conversion of hydrogen peroxide in the range of 50% to 100%, preferably from 80% to 99.8%, is achieved.
  • the reaction conditions are preferably selected such that the components used in the molar deficit of the components allyl chloride and hydrogen peroxide is reacted to 70% to 100%, preferably to 90% to 99%.
  • the reaction in steps a) and d) is carried out continuously in a fixed bed reactor, wherein a mixture containing hydrogen peroxide, optionally solvent and allyl chloride or the mixture (A2), over a fixed bed of the titanium-containing
  • the fixed-bed reactor used is preferably a tubular reactor cooled from the outside, in particular a tube-bundle reactor.
  • the fixed bed reactor can be operated in both upflow and downflow, with downflow operation in the trickle bed state being preferred.
  • the reaction can be carried out in two or more reactors connected in series.
  • two reactors connected in series are used.
  • two or more reactors arranged in parallel can be used, so that a reactor for catalyst regeneration can be taken out of operation and the reaction can be continued in a reactor connected in parallel.
  • Reaction mixture is separated in step b) of the process according to the invention in a distillation in a mixture (A) containing unreacted allyl chloride, and 1-chloropropane and / or 2-chloropropane and a
  • the distillation is preferably carried out as a continuous rectification, wherein a rectification column is fed in a middle section of the reaction mixture formed in the first reaction stage, at the top of the
  • the mixture (A) is removed and from the bottom of the column, the mixture (B) is removed.
  • a rectification column with 10 to 50 theoretical plates is used. The rectification is preferably carried out at a pressure at the top of the column in the range of 0.2 to 3 bar and preferably at a reflux ratio of 0.5 to 5.
  • the distillation is preferably conducted so that the resulting mixture (A) contains more than 95% of the allyl chloride contained in the feed reaction mixture, and the resulting mixture (B) contains more than 95% of the epichlorohydrin contained in the feed reaction mixture.
  • step c) of the process according to the invention the mixture (A) is divided into a mixture (Al) which is recycled to the first reaction stage and a mixture (A2) which is fed to the second reaction stage.
  • the mixture (A) is divided so that 50% to 98%, more preferably 70% to 95% of the allyl chloride contained in the mixture (A) with the mixture (Al) is recycled to the first reaction stage.
  • the mixture (A) is separated by distillation, so that the in Mixture (A) contained chloropropanes in the mixture (A2) are enriched.
  • step e) of the process according to the invention the reaction mixture formed in the second reaction stage is separated in a distillation into a mixture (C) containing 1-chloropropane and / or 2-chloropropane and a mixture (D) containing epichlorohydrin.
  • the distillation is preferably carried out as a continuous rectification, wherein a rectification column is fed in a middle section of the reaction mixture formed in the second reaction stage, at the top of the column mixture (C) is removed and from the bottom of the column, the mixture (D) is removed ,
  • a rectification column with 10 to 50 theoretical plates is used.
  • the rectification is preferably carried out at a pressure at the top of the column in the range of 0.5 to 3 bar and preferably at a reflux ratio of 0.5 to 5.
  • the distillation is preferably operated so that the resulting mixture (C) contains more than 90% of the chloropropanes contained in the feed reaction mixture and the resulting mixture (D) contains more than 95% of the epichlorohydrin contained in the feed reaction mixture.
  • the mixture (D) obtained in step e) of the process according to the invention is recycled to the first reaction stage.
  • This embodiment is particularly advantageous when hydrogen peroxide is used in molar excess in step d) and the mixture (D) is still unreacted
  • steps d) and e) of the process according to the invention take place simultaneously in the form of a reactive distillation.
  • the titanium-containing zeolite catalyst of the second reaction stage is disposed in a reaction section of a rectification column, the mixture (A2) is fed to the column at a point below the reaction section, and hydrogen peroxide is supplied at a point above the reaction section.
  • the mixture (C) is removed and from the bottom of the column, the mixture (D) is removed.
  • Figure 1 shows schematically a preferred embodiment of the claimed process in which the reactions in steps a) and d) are carried out in fixed bed reactors and the distillations in steps b) and e) are carried out in distillation columns. Not shown are required for carrying out the process auxiliary equipment, such as pumps, heat exchangers, evaporators and
  • Capacitors In the process of FIG. 1, nitrogen is additionally fed as inert gas in steps a) and e) in order to prevent the formation of combustible gas mixtures. Hydrogen peroxide (1), allyl chloride (2), methanol (3) and nitrogen (4) are fed to the first fixed bed reactor (a). The reaction mixture obtained in the first fixed bed reactor (a) is used in the
  • Epichlorohydrin contains (mixture B), and an exhaust gas stream (6).
  • the mixture A is then divided into (c) into a stream (8) which is recycled to the first fixed bed reactor (a) (mixture Al) and a stream (9) which is fed to the second fixed bed reactor (d) (mixture A2) and there with further hydrogen peroxide (10) is reacted.
  • the reaction mixture obtained in the second fixed bed reactor (d) is separated in the distillation column (e) into a top product (12) containing the chloropropanes (mixture C) and a bottom product (13) containing epichlorohydrin (mixture D) and into the first Fixed bed reactor (a) is returned.
  • the distillation column (e) is additionally fed nitrogen (11).
  • Allyl chloride was reacted with hydrogen peroxide in methanol as solvent using a titanium silicalite catalyst of MFI structure. The reaction took place in two tubular reactors connected in series, which were cooled by a cooling jacket. The catalyst was used as a fixed bed in the form of extrudates. The first reactor contained 21.5 g of catalyst, the second reactor 20.7 g. Allyl chloride and a mixture of an aqueous hydrogen peroxide solution and methanol were continuously supplied to the first reactor. The metered flow rates, the composition of the mixture and the molar ratio of allyl chloride to hydrogen peroxide in the educts are shown in Table 1.
  • the reactors were operated in an upward flow mode, the pressure in the reactors being kept at 7 to 8 bar and the first reactor was heated to 36 ° C. and the second reactor to 38 ° C.
  • the content of hydrogen peroxide was determined by redox titration and the contents of allyl chloride and epichlorohydrin by gas chromatography.
  • the turnover calculated from these contents Hydrogen peroxide and selectivities for epichlorohydrin relative to reacted allyl chloride are shown in Table 1.
  • Table 1 shows that with increasing molar excess of allyl chloride, the selectivity for epichlorohydrin increases.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

Procédé de fabrication d'épichlorhydrine, dans lequel, dans une première étape de réaction, un chlorure d'allyle contenant des chloropropanes en excès est mis à réagir avec du peroxyde d'hydrogène. Le chlorure d'allyle n'ayant pas réagi est séparé et renvoyé à la réaction, une partie du chlorure d'allyle séparé étant envoyée à une deuxième étape de réaction et étant mise à réagir avec du peroxyde d'hydrogène, la quantité de peroxyde d'hydrogène dans la deuxième étape de réaction étant choisie de façon que le chlorure d'allyle soit presque complètement converti. Les chloropropanes sont séparés par distillation du mélange réactionnel de la deuxième étape de réaction et prélevés du procédé.
PCT/EP2008/067584 2008-03-17 2008-12-16 Procédé de fabrication d'épichlorhydrine Ceased WO2009115152A1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US12/919,637 US8481765B2 (en) 2008-03-17 2008-12-16 Method for the production of epichlorohydrin
ES08873464T ES2379311T3 (es) 2008-03-17 2008-12-16 Procedimiento para la preparación de epiclorhidrina
EP08873464A EP2285791B1 (fr) 2008-03-17 2008-12-16 Procédé de fabrication d'épichlorhydrine
CN2008801281503A CN101983192B (zh) 2008-03-17 2008-12-16 表氯醇制备方法
BRPI0822343-2A BRPI0822343A2 (pt) 2008-03-17 2008-12-16 Processo para a preparação de epicloroídrina
HK11105877.4A HK1152034B (en) 2008-03-17 2008-12-16 Method for the production of epichlorohydrin
PL08873464T PL2285791T3 (pl) 2008-03-17 2008-12-16 Sposób wytwarzania epichlorohydryny
AT08873464T ATE548361T1 (de) 2008-03-17 2008-12-16 Verfahren zur herstellung von epichlorhydrin
AU2008353129A AU2008353129B2 (en) 2008-03-17 2008-12-16 Method for the production of epichlorohydrin
JP2011500055A JP5615797B2 (ja) 2008-03-17 2008-12-16 エピクロロヒドリンの製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08102653.6 2008-03-17
EP08102653A EP2103604A1 (fr) 2008-03-17 2008-03-17 Procédé de fabrication d'épichlorhydrine

Publications (1)

Publication Number Publication Date
WO2009115152A1 true WO2009115152A1 (fr) 2009-09-24

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ID=39495151

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Application Number Title Priority Date Filing Date
PCT/EP2008/067584 Ceased WO2009115152A1 (fr) 2008-03-17 2008-12-16 Procédé de fabrication d'épichlorhydrine

Country Status (13)

Country Link
US (1) US8481765B2 (fr)
EP (2) EP2103604A1 (fr)
JP (1) JP5615797B2 (fr)
KR (1) KR20100124300A (fr)
CN (1) CN101983192B (fr)
AT (1) ATE548361T1 (fr)
AU (1) AU2008353129B2 (fr)
BR (1) BRPI0822343A2 (fr)
ES (1) ES2379311T3 (fr)
PL (1) PL2285791T3 (fr)
RU (1) RU2456279C2 (fr)
TW (1) TWI427072B (fr)
WO (1) WO2009115152A1 (fr)

Cited By (2)

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Publication number Priority date Publication date Assignee Title
US8859790B2 (en) 2010-02-02 2014-10-14 Momentive Specialty Chemicals Inc. Process for the manufacture of a 1,2-epoxide and a device for carrying out said process
EP2796452A1 (fr) 2013-04-23 2014-10-29 Momentive Specialty Chemicals Research Belgium S.A. Procédé d' élimination de 1,2-époxy-5-hexène d'épichlorhydrine

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EP2149569A1 (fr) * 2008-08-01 2010-02-03 Hexion Specialty Chemicals Research Belgium S.A. Procédé de fabrication d'un 1,2-epoxyde
EP2149570A1 (fr) * 2008-08-01 2010-02-03 Hexion Specialty Chemicals Research Belgium S.A. Procédé de fabrication d'épichlorhydrine avec peroxyde d'hydrogène et un complexe manganèse
RU2593205C1 (ru) * 2015-06-10 2016-08-10 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Чувашский государственный университет имени И.Н. Ульянова" Способ выделения концентрированного эпихлоргидрина из продуктов эпоксидирования хлористого аллила пероксидом водорода на титансодержащем цеолитном катализаторе
CN111574481A (zh) * 2020-05-29 2020-08-25 中国科学院理化技术研究所 一种制备环氧氯丙烷的方法

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